LOBELANIDINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H29NO2.ClH
Molecular Weight	375.932
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CN1[C@@H](C[C@@H](O)C2=CC=CC=C2)CCC[C@H]1C[C@H](O)C3=CC=CC=C3

InChI

InChIKey=IDPAEJSVXMLVBS-NRDKKTCLSA-N

InChI=1S/C22H29NO2.ClH/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18;/h2-7,9-12,19-22,24-25H,8,13-16H2,1H3;1H/t19-,20+,21-,22+;

HIDE SMILES / InChI

Molecular Formula	C22H29NO2
Molecular Weight	339.4712
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24636059
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19217305 | https://www.ncbi.nlm.nih.gov/pubmed/17658751

Lobelanidine is one of lobelia alkaloids that are the constituents of Lobelia inflata. Lobelia Chinensis Lour. (L. chinensis) is a plant of the Campanulaceae family that is commonly known as "xi-mi-cao", and "she-she-cao". It has been widely used as an antidote, diuretic, and hemostat in traditional Chinese medicine for decades. Lobelanidine is known for its emetic and anticancer activity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Neuronal acetylcholine receptor subunit alpha-7 14 Target ID: P36544 Gene ID: 1139\|\|\|89832 Gene Symbol: CHRNA7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26434115	Partial Agonist 290
Neuronal acetylcholine receptor; alpha3/beta4 40 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26434115	Partial Agonist 290	300.0 nM [Ki]
Neuronal acetylcholine receptor; alpha3/beta4 40 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26434115	Partial Agonist 290
Matrix metalloproteinase 9 20 Target ID: CHEMBL321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28987294	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24636059	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis of (-)-lobeline via enzymatic desymmetrization of lobelanidine.	2009 Mar 1	19217305

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:06:11 GMT 2023` Edited by `admin` on `Sat Dec 16 10:06:11 GMT 2023`
Record UNII	7F7I5P820F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOBELANIDINE HYDROCHLORIDE

Common Name

English

2,6-PIPERIDINEDIETHANOL, 1-METHYL-.ALPHA.2,.ALPHA.6-DIPHENYL-, HYDROCHLORIDE (1:1), (.ALPHA.2R,.ALPHA.6S,2R,6S)-REL-

Systematic Name

English

LOBELANIDINE HYDROCHLORIDE [MI]

Common Name

English

Code System Code Type Description

CAS

6112-86-3